RemoteWoman

Head of Sales Enablement

RemoteWoman

full-time

Posted on:

Origin:  • 🇨🇦 Canada

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Job Level

Lead

Tech Stack

CloudOpen Source

About the role

  • Build the sales enablement framework from the ground up, creating scalable programs, playbooks, and training paths.
  • Accelerate sales productivity by boosting seller confidence in product, process, and positioning - driving stronger performance across segments.
  • Stay hands-on during implementation - coaching, mentoring, and guiding sellers as they adopt new tools and approaches.
  • Partner with Product, Marketing, Engineering, and Customer Success to ensure enablement stays aligned with launches, market shifts, and customer signals.
  • Strengthen onboarding and ramp programs to reduce time-to-productivity and ensure new hires are confident early.
  • Translate product usage data into actionable sales plays, teaching teams how to spot and act on product-led opportunities.
  • Define, track, and report enablement KPIs, communicating clear outcomes and opportunities to executives.
  • Connect product insights to sales execution, aligning go-to-market teams with the way customers actually buy and giving sellers the confidence to succeed from day one.

Requirements

  • 7+ years of experience in sales enablement and direct sales within a technology-driven environment.
  • Depth in modern sales motions, including PLS, value selling, and a variety of customer-centric methodologies (e.g., MEDDICC, SANDLER, CHALLENGER).
  • Proven ability to design enablement frameworks while staying close enough to coach and mentor teams through adoption.
  • Strong communication and storytelling skills - able to distill complex product and market insights into clear, actionable guidance for sellers.
  • Hands-on experience with enablement technologies (LMS or equivalent), with a practical approach to scaling.
  • Program and project management discipline—comfortable balancing multiple initiatives while staying focused on measurable outcomes.
  • A collaborative, team-first mindset with the confidence to align cross-functionally and influence without unnecessary noise.
  • Legally authorized to work in Canada, France, Germany, Spain, the United Kingdom, or the United States; visa sponsorship not available.
  • All roles require background checks.